Palladium(0)-Catalyzed Heteroannulations of Allenamides: General Synthesis of δ-Carbolines and Benzofuro[3,2-<i>b</i>]pyridines
Debasmita Mondal, Subhendu Pramanik, Chinmay Chowdhury
Abstract
Palladium(0)-catalyzed reactions between allenamides 3 or 4 and aryl iodides/bromides 5/6 provide an easy access to δ-carbolines 1 or benzofuro[3,2-b]pyridines 2. The reaction constitutes a fast intermolecular assembly that takes place in one pot, and the choice of the phosphine ligand is critical for success. A plausible reaction mechanism is proposed. The reaction is amenable to the synthesis of bis-heteroannulated products.
Topics & Concepts
ChemistryPalladiumCatalysisPhosphineIntermolecular forceCombinatorial chemistryArylLigand (biochemistry)Medicinal chemistryOrganic chemistryMoleculeAlkylBiochemistryReceptorSynthesis and bioactivity of alkaloidsCatalytic C–H Functionalization MethodsCatalytic Alkyne Reactions